Methyl iodide → 4-Ethylquinolin-2(1H)-one

To a suspension of 4-methylquinolin-2(1H)-one (5 g, 31 mmol) in anhydrous tetrahydrofuran (100 mL) under a nitrogen atmosphere cooled in an acetone/dry ice bath was added dropwise by syringe a 1.6N solution of n-butyl lithium in hexanes (49 mL, 78 mol). The resulting solution was warmed to r.t. for 2 h at which time iodomethane (3 mL, 47 mmol) was added by syringe. The reaction mixture was stirred at r.t. for 0.5 h then cooled in an ice bath. The reaction mixture was quenched by the addition of aq. 2N HCl and then extracted with excess chloroform. The combined organic extracts were washed with saturated sodium bicarbonate, dried over sodium sulfate, filtered and the solvent removed under vacuum to provide a solid.

1. temperaturecooled in an acetone/dry ice bath
2. additionwas added by syringe
3. temperaturethen cooled in an ice bath
4. customThe reaction mixture was quenched by the addition of aq. 2N HCl
5. extractionextracted with excess chloroform
6. washThe combined organic extracts were washed with saturated sodium bicarbonate
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. customthe solvent removed under vacuum
10. customto provide a solid

ORD record

ord-24b8824ab261437ea36ec379f8556894

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07084156B2